Issa Rae Sounds Off on Dating Apps, Fashion Week, and Cupping

By
Photography Noua Unu
Stylist Sean Knight

Published April 8, 2020

Bodysuit and Gloves by Gucci. Pants and Belt Stylist’s Own. Earrings by Cactus de Cartier.

Issa Rae is in takeover mode. Any trace of the newcomer who launched her career in 2011 with the web series The Misadventures of Awkward Black Girl is gone. This month alone, the writer, actor, and producer is premiering the fourth season of her Peabody Award-winning HBO show Insecure, while also starring opposite Kumail Nanjiani in the romantic caper The Lovebirds. But Rae wants more: Last year, the 35-year-old Los Angeles native partnered with Atlantic Records to form her own label, Raedio. Before going on to conquer the rest of the entertainment industry, she paused to provide a few thoughts on 19 topics chosen at semi-random.

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MEGAN THEE STALLION

“Exudes sex appeal and coolness. She’s a bad bitch and her free-styles are my favorite thing about her. Her flow is just incredible.”

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NANCY PELOSI

“She’s headstrong and she’s petty. Petty Pelosi.”

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DATING APPS

“Don’t know them, don’t use them. I’m sure they’re helpful for a lot of people, but they seem to me to be hookup apps. Shout-out to people who found love.”

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LOW-RISE JEANS

“Fuck low-rise jeans. They’ve never been for me. But for the flat-belly bitches out there, good for you.”

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CRAFT SERVICE

“The key to my heart and the only reason I go to work.”

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CUPPING

“I don’t know what that is, but it sounds like sexual harassment.”

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NETWORKING

“A necessary evil. The best networking is natural, but when you go with the intent to pitch something, it’s aggravating. Nobody wants that. Nobody wants it to feel like business, business, business, business.”

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INGLEWOOD

“Always up to no good. A lot of people think I’m from Inglewood, but I’m not. My show is partially set there, so I rep it all day.”

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MOESHA

“My inspiration to this day. No teenage black female character has resonated with me as much.”

Issa Rae

Jacket, Skirt, and Shoes by Prada. Earrings by Cactus de Cartier. Ring by Cartier Maillon Infini.

NETWORK TV

“It’s got to catch up and revamp because it’s falling behind.”

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SHONDA RHIMES

“Singlehandedly responsible for a resurgence in network TV, but even she peaced out. Shout-out to Shonda, who is an inspiration to me and who took a chance on me when I needed one.”

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L.A. TRAFFIC

“The devil, although I use the time to get those calls in. I hate being on the phone, but there’s no better time to do it than when I’m in traffic.”

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ACCEPTANCE SPEECHES

“Acceptance speeches should always have a mix of humor and earnestness. Is it ‘earnestness’ or ‘earnesty’?”

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CRUSHES

“I support them.”

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FRONT ROW AT FASHION WEEK

“Give a bitch some shoulder room!

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DONALD GLOVER

“A hero. I’ve always admired him, since he made Mystery Team with Derrick Comedy. He’s always ahead of the curve.”

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EXTRAS

“Shout-out to the TV show Extras by Ricky Gervais. It’s a good-ass show because, extras, y’all are weird as fuck sometimes.”

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PASSWORD SHARING

“Don’t do it. The only time you should share your password is in case of death, and in that case, it should be to delete everything.”

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ROTTEN TOMATOES

“Very convenient.”

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Hair: FELICIA LEATHERWOOD
Makeup: JOANNA SIMKIN at THE WALL
Manicure: SHAUNA URSERY
Hair Assistant: BREANA WARD